20+ Great Retirement Songs for Teachers


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Teachers and principals are some of the most valued members of any community. Every year they meet unique and beautiful human beings, each with their own hopes and dreams.

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As mentors, many teachers spend their careers being guides and counselors to each and every one of those kids. That’s what makes retirement from this profession not only a remarkable milestone but an affirmation of an educator's strength and exceptional character.

For that reason, the list below is a particularly diverse selection of songs to play at a retirement party. Hopefully, one of them will speak to you and your or your loved one's long career. In part, they were also chosen to provide a full and unique playlist, so that anyone attending will find something relatable.

Tip: Retirement parties are fun and upbeat. Unfortunately, growing older often comes with the loss of family members and close friends as they grow old, too. You can help a retiree deal with that kind of loss by sharing this post-loss checklist with them. 

Best Retirement Songs for Teachers

The list of songs below is wide-ranging from the classic songbirds like Frank Sinatra to rock legends like Aerosmith or The Grateful Dead. Most are meant to provide a good, light-hearted look into wild Mondays or keep any backyard gathering upbeat and fun.

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1. "Young at Heart" by Frank Sinatra

Fluttery strings, soft woodwind, and a drum brush accompany Frank Sinatra’s iconic voice. If you decide to add a touch of class and to your retirement party playlist, then opt for "Young at Heart."

2. "When I’m Sixty-Four" by The Beatles

Perceptions have changed a bit since this song was first released, because "When I'm Sixty-Four" sounds more like how people act when they're eighty or ninety.

Even so, I've known some pretty spry octogenarians and nonagenarians. Just the same, it’s a sweet song about unusual love through the ages. 

3. "Blue Skies" by Willie Nelson

If you're a fan of Willie Nelson, then perhaps you'll agree that this song matches his inclination towards simplicity. "Blue Skies" has a lot of repetition in the lyrics, but the accompanying music has a life of its own. 

4. "Touch of Grey" by The Grateful Dead

For those who are in the public eye, aging can be a mass of unwanted commentary that no one appreciates hearing. The Grateful Dead wrote this song in response to those unfeeling critics to make themselves feel better.

5. "Come Sail Away" by Styx

This ballad-producing arena-rock band of the 70s is credited with composing long-lasting classics like "Come Sail Away" and “Babe.”

While the band members were plagued by diseases such as HIV and cirrhosis, as well as a host of other physical ailments, they still rose to acclaim among their fans, despite their many critics.

6. "Walk This Way" by Aerosmith

What's your swagger going to look like now that the stress of a class schedule is gone? Maybe this song will help you discover a new way of letting others how good life can be.

7. "Under Pressure" by Queen

The stresses, overloading, and punching of timecards are over. With that, Queen’s song evokes a kind of understanding and need that you’ve got to discover time for finding some moments that calm your heart, sleep a little more, and your true passions. 

8. "Manic Monday" by The Bangles

One of the most interesting facts about this song is that it was written by Prince. The Bangles grabbed hold of these lyrics and turned the song into the classic “Mondays are awful” kind of song. This works for teachers who know the agony of class the very next morning after a vacation.

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9. "Last Train to Clarksville" by The Monkees

"Last Train to Clarksville" works as a retirement song for teachers if there’s a little protest in you.

While The Monkees couldn’t explicitly protest the Vietnam War, they could make their opinions known for the struggle and apprehension that soldiers were facing.

10. "My Generation" by The Who

As a teacher, you have given your life to helping students find a place in time and society. Whether the lyrics in this song matter more today than yesterday, you were still a powerful beacon in the lives of kids who needed some hope and guidance.

11. "Celebration" by Kool & The Gang

Nothing comes close to "Celebration" for post-disco upbeat vibes. While the song doesn’t reference any “end of the road” achievements or milestones, it’s appropriate because it is celebratory in all the best ways possible.

Funny Retirement Songs for Teachers

While humor is subjective, enjoying oneself is a universal desire. So, whether it’s your job to build the playlist or to just enjoy the party, settle in and appreciate some songs meant to bring a smile to your face.

12. "Yakety Yak" by The Coasters

The song "Yakety Yak" may technically be about some teenage angst, but there’s a relatable aspect to it, too.

We all have a similar meter in our brains where the needle starts twitching uncontrollably to the right when the same voice in the same tone is nothing but repetitive orders and problems.

13. "I Can’t Get No (Satisfaction)" by The Rolling Stones

Whether or not you're re retiring, this sentiment is one that everyone can understand! Plus, everyone seems to know at least a few of the lines by heart regardless of their age. Go ahead, put it in the queue and see who belts out the refrain with you.

14. "Drink in My Hand" by Eric Church

If you've lived nothing but 40-hour weeks filled with stress day after day, then you'll appreciate Eric Church's "Drink in My Hand."

This song also works well for those teachers who love exploring the craft brewery and wine industry popping up all over the US, too.

15. "Tik-A-Tee, Tik-A-Tay" by Dean Martin

If you’re envisioning a movie with Walter Matthau and Jack Lemmon causing chaos while having a good laugh, then you’ve got the feeling for this song down pat. So, make sure to include it during your outdoor retirement party and watch how people smile and sway.

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16. "Take This Job and Shove It" by Johnny Paycheck

The one song that is on everyone's disgruntled playlist is "Take This Job and Shove It." Nearly everyone has had at least one of these jobs in their life.

17. "Little Old Lady (from Pasadena)" by Jan and Dean

There are two rites of passage when you reach the privilege of senior citizenship.One is experiencing the most authentic freedom of speech ever—the other is driving terribly.

So since you've only just retired, you've got a lot of time to start practicing for those glory days now. 

18. "Happy Trails" by Roy Rogers

"Happy Trails" is a song most often parodied in retirement. So, it’s the perfect little goading song to sneak onto someone’s playlist even though they’re only retiring. 

19. "We’re Not Gonna Take It" by Twisted Sister

Turning on the radio in the 80s meant metal music from those with crimped Aqua Net hair, leather pants, and generous eye makeup.

As such, that means you also know Twisted Sister sang the most resonating I’m-outta-here goodbye song ever. Go on, turn it up and get some pep in your step on the way out the door.

20. "No Shirt, No Shoes, No Problem" by Kenny Chesney

Now that you have retired and your bucket list wish in life is to be somewhere warm and on a beach, this might be your new theme song. Just as Kenny Chesney warbles: no problem.

21. "Margaritaville" by Jimmy Buffet

This song has a split personality of a classic hoop-it-up coupled with a mellow out song. On the one hand, you have the universal call sign for tequila. On the other, you have the classic tune for wasting idly away.

Reaching a Milestone

By and far, teaching is one of the hardest and emotionally draining professions out there. Hopefully, after giving your heart to thousands of students throughout your career, you can put your head into the journey that lies ahead. Congratulations!

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